Happy Sunday, friends!

I spent years working toward freedom, assuming I’d know what to do once I had it.

Now I have money, control over my time, and more options than I ever expected.

Somehow, it felt easier to know what I wanted when I couldn’t have everything.

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Some thoughts on money, where to live, and missing the simplicity of having fewer options

A few years ago, I had a normal 9–5 as a civil engineer.

I had less money, less freedom, and fewer options. Where I lived was partly decided by where I worked. Most of my week was already spoken for.

And I was happy.

I wanted more, obviously. I wanted enough money to stop organizing my life around a job. I wanted to travel when I felt like it, work on things I cared about, and choose where to live. For those of you who have followed my journey since 2018, you know that I was a part of the FIRE journey for a long time, which was insanely motivating. Eventually, I reached goal after goal after goal.

And now I have a lot of that freedom.

What I didn’t expect was how much time I’d spend wondering what to do with it.

Where should I live? What should I work on? How much should I work at all? Should I keep pushing, or actually enjoy what I spent all those years trying to get?

These are good problems to have. I know that.

They still take up a surprising amount of space in my head.

I recognized more of myself in this than I wanted to

Vinay Hiremath, the co-founder of Loom, published a post called “I am rich and have no idea what to do with my life.”

Near the beginning, he wrote:

“I have infinite freedom, yet I don’t know what to do with it.”

That sentence stayed with me.

He described struggling to walk away from a $60 million pay package even though he already had more money than he knew what to do with. After leaving, he explored starting a robotics company, then admitted that part of the appeal was wanting to look like Elon Musk.

I appreciated how embarrassing he was willing to make it sound.

He admitted he didn’t really know what he wanted, and that some of the things he thought he wanted were tied to how he wanted other people to see him.

That’s harder to admit than “I’m taking some time off.”

My situation is different from his. But I recognize the feeling of reaching a position you wanted for years and realizing you haven’t thought very clearly about what happens afterward.

You spend so long trying to get more options that you assume choosing between them will be the easy part.

I thought I knew what I wanted

When I had a 9–5, the goal felt fairly obvious.

Make money. Invest. Build something on the side. Get to a point where I didn’t have to ask permission to use my own time.

Back then a free afternoon felt like a free afternoon. I didn’t need to ask whether I was using my freedom properly.

Now, even enjoying myself can turn into a decision I feel I should research more.

Could I be somewhere better? Should I be building something? Am I getting too comfortable? Will I regret not doing more while I have the chance?

There’s something quite stupid about working toward freedom and then making yourself feel guilty for having it.

Yet here we are.

Where to live becomes a much bigger question

Where to live is probably the clearest example.

When money and work limit your options, you make compromises because you have to. You live near your job. You choose the apartment you can afford. You stay somewhere because that’s where your life already is.

Once those limits loosen, almost everything becomes negotiable.

I could stay in my hometown. I could spend more time somewhere warmer. I could move somewhere with a better tax setup, a bigger international crowd, or more people working on things I find interesting.

Then I start comparing.

Weather. Housing. Taxes. Walkability. Friends. Restaurants. Flights. How easy it is to meet people. Whether I’d actually like being there in February.

All reasonable things to consider.

The problem is that each place comes with a different imagined life.

In one, I’m more social. In another, I’m healthier. Somewhere else, I’m more focused and ambitious, like a full-time trader and really making a huge career out of it. Another version of me spends less time online and plays more tennis. Another version is just reading books all day, and the rest of the time I am writing.

Of course it’s hard to choose when I’m asking a city to settle all of that.

And I’m usually comparing my actual life, including its boring days, with a version of another place where somehow I’ve fixed all my habits.

I don’t picture myself sitting in a nicer apartment, looking at the same phone, wondering where to go next.

I probably should.

The pressure to make freedom worth it

I keep coming back to the phrase “sudden wealth syndrome.”

I’m not diagnosing myself. My life changed over years, and I’m not trying to turn uncertainty into a medical condition.

But I recognize something in the idea: my financial circumstances changed faster than my understanding of how I wanted to live.

For years, more money was an easy thing to want.

It gave me something concrete to work toward. I could measure progress. Even when I wasn’t satisfied, I had a pretty clear explanation for what was missing.

Another good year would be nice. More money would still have uses. But I can’t honestly tell myself that a higher number will decide where I belong or what I want an ordinary week to look like.

Ok, so this is the core problem. Say that you have an extremely high-status job and earn $200k per year. That’s great when you are at $0 or below $1m. But after that, the money starts to have diminishing returns.

You could read my full thoughts on that in the tweet below that went viral on Twitter:

To summarize it they call it no-man’s land of wealth or 7-figure hell, and it’s basically when you are too poor to retire, but too rich to really need a normal job.

Anyway, there’s a strange pressure that comes with being able to choose.

If I can live almost anywhere, why haven’t I found the right place?

If I can choose exactly what to do every day, then why am I not constantly happy?

If I have time, why haven’t I done all the things I said I’d do when I had time?

I can make myself feel behind without anyone else being involved.

The advice is hard to use

When I talk to friends about this, they usually have advice.

Move somewhere warm. Take a year off. Start something new. Stop overthinking it and enjoy the money. Put it all in index funds and do nothing. Just enjoy life, man.

I know they mean well. And from the outside, I can see why it looks simple. I probably would’ve given the same advice a few years ago.

But most of them are answering from where they are now. They still have the constraints I used to have, so their advice naturally starts with what they’d do if those constraints disappeared.

When you work a job you don’t like, the only thing you want is freedom. You want vacation, you want everything you don’t have right now. But IMO I’ve had freedom/vacation constantly for 6 years now; I don’t need more time to relax/do nothing. I am still hungry; I like to learn, build, research, etc.

My friends know me, so I want to hear what they think. But they can’t tell me what I’ll find satisfying once the things they’re still working toward are already available to me.

And honestly, I sometimes want their advice to do more than it can. I want someone who knows me to say, “Do this,” and feel certain enough that I can stop going back and forth.

I’m not sure anyone can give me that.

I’m good at finding reasons

Crypto makes this especially awkward.

I spend a lot of time looking at what could happen next. New projects, new narratives, new opportunities. There’s usually another reason to stay interested.

I enjoy that. I don’t want to pretend otherwise.

But I also know how easily I can build a convincing argument for something once it has my attention.

I can do it with an investment. I can do it with a business idea. And apparently I can do it with a city.

Choosing means letting some things go

There’s a point where keeping every option open becomes its own decision.

If I’m always considering the next place, it’s harder to put down roots in this one. If every project is provisional, it’s harder to stay with it through the parts that aren’t immediately rewarding.

I can tell myself I’m being flexible. Sometimes I am.

Other times, I just don’t want to feel the disappointment of choosing something and discovering it isn’t perfect.

So I keep looking.

I don’t have a neat ending for this

I’m grateful for the money.

It has made my life better in very real ways. I can make decisions I couldn’t make before, and walk away from things I don’t want to do.

I also miss how straightforward wanting more used to feel.

That’s an awkward thing to admit publicly, especially when the thing I’m struggling with is having choices other people would love to have.

But I’d rather be honest about it than act as if reaching a financial goal made me certain about everything else.

I’m still figuring out where I want to live. I’m still figuring out how much ambition I want in my life, and how much of it I genuinely enjoy.

For now, I want to stop treating every choice as a verdict on the rest of my life.

Choose somewhere. Spend enough time there to know it. Do work I’m interested in. Make plans with people I want to see again.

And when I have a good day, try to let it be a good day without checking whether I could have had a better one somewhere else.

…

Until next time,

Ciao.